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WO1994013748A1 - Traitement de surface antimicrobien durable de materiaux plastiques - Google Patents

Traitement de surface antimicrobien durable de materiaux plastiques Download PDF

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Publication number
WO1994013748A1
WO1994013748A1 PCT/US1993/011406 US9311406W WO9413748A1 WO 1994013748 A1 WO1994013748 A1 WO 1994013748A1 US 9311406 W US9311406 W US 9311406W WO 9413748 A1 WO9413748 A1 WO 9413748A1
Authority
WO
WIPO (PCT)
Prior art keywords
acid
coating material
quaternary ammonium
solution
article
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US1993/011406
Other languages
English (en)
Inventor
Richard P. Heggs
Virginia M. Northrup
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Warner Lambert Co LLC
Original Assignee
Warner Lambert Co LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Warner Lambert Co LLC filed Critical Warner Lambert Co LLC
Priority to AU56759/94A priority Critical patent/AU5675994A/en
Publication of WO1994013748A1 publication Critical patent/WO1994013748A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D177/00—Coating compositions based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Coating compositions based on derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/16—Halogen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/544—Silicon-containing compounds containing nitrogen

Definitions

  • the invention is directed to improved antimicrobial surface treatments for plastic materials .
  • Antimicrobial coatings have many uses in textiles and other materials that are exposed to microbial contamination. One such use is with toothbrushes. Modern toothbrushes are made out of thermoplastic materials and typically have bristles made from an appropriate thermoplastic material such as nylon.
  • toothbrushes can, under the proper conditions of heat and humidity, develop into sources of the very microbial agents that they are used to combat. Others have attempted to control this tendency to contamination by coating the nylon bristles with antibacterial or antimicrobial agents. Coating of the bristles, however, has not generally proven effective for continued antimicrobial activity. The bristles of a toothbrush are exposed to high abrasion levels, and any coating generally wears off after only a few uses of the toothbrush. After the coating is sufficiently worn to expose part of the underlying fiber, the toothbrush is susceptible to contamination.
  • the invention comprises a coating material comprising a nylon multipolymer resin, an acid and a silane quaternary ammonium solution.
  • the invention comprises a method of providing antimicrobial protection for a coated article, comprising the ⁇ steps of acid etching the article to be coated and applying to the etched article a coating material comprising a nylon multipolymer resin, an acid and a silane quaternary ammonium solution.
  • the invention comprises a coating material comprising a nylon multipolymer resin, an acid and a silane quaternary ammonium solution. These ingredients may be combined in a solvent to form a suspension or solution, and the article to be coated may be dipped or otherwise painted with the coating solution. The coating is then preferably dried before use.
  • the nylon multipolymer resin preferably comprises Elvamide 8061, a nylon multipolymer resin manufactured by DuPont Polymers, Wilmington, Delaware.
  • Elvamide is a nylon multipolymer resin comprising polyamides. It is soluble in alcohol.
  • the acid is preferably a mineral acid such as hydrochloric acid or an organic acid such as acetic acid.
  • the silane quaternary ammonium compound is preferably 3 (trimethoxysilyl) propyloctadecyl dimethyl ammonium chloride: Preferably, this compound is Dow Corning 5700 Antimicrobial Agent, manufactured by Dow Corning Corporation, Midland, Michigan.
  • the three components may be dissolved or suspended in a suitable solvent such as methanol or another alcohol, and articles to be coated may be painted with or dipped in the solution.
  • a suitable solvent such as methanol or another alcohol
  • articles to be coated comprise thermoplastic materials, and more preferably comprise materials that have an affinity for the coating solution.
  • materials that have an affinity for the coating solution are nylon and cellulose acetate propionate.
  • the materials to be coated are preferably acid etched before exposure to the coating solution.
  • Hydrochloric acid and methanol are a preferred combination for the etching agent, but other suitable agents are known in the art for etching thermoplastic materials.
  • the coated articles may be dried at room temperature or at elevated temperature.
  • Nylon 6-12 plaques were suspended in the 50 degrees C quat solution for a total of one hour and cured in a 150 degrees F oven for two hours.
  • a portion of the cured plaques were scrubbed using a brush with a cleaning solution. Both scrubbed and unscrubbed plaques were tested for antimicrobial activity and gave a greater than one log kill when compared to a control.
  • Nylon 6-12 plaques were acid etched for 60 seconds in a 10 volume percent hydrochloric acid (37%) and methanol solution.
  • a portion of the cured plaques was scrubbed using a brush with a cleaning solution. Both scrubbed and unscrubbed plaques were tested for antimicrobial efficacy and gave a greater than one log kill when compared to a control.
  • CAP plaques were suspended in the above solution at room temperature for 60 minutes. The plaques were air dried for thirty minutes and cured in a 120 degrees F oven for two hours. A portion of the cured plaques was scrubbed using a brush with a cleaning solution. Both scrubbed and unscrubbed plaques were tested for antimicrobial efficacy and gave a greater that one log kill when compared to a control.
  • CAP Cellulose Acetate Propionate
  • Nylon plaques were suspended in the solution for one hour, air dried for fifteen minutes and cured in a 55 degree C oven for one hour.
  • a portion of the cured plaques was scrubbed using a brush with a cleaning solution. Both the scrubbed and unscrubbed plaques were tested for antimicrobial efficacy. The unscrubbed plaques gave a greater than three log kill when compared to a control. The scrubbed plaques showed no efficacy compared to the control.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Plant Pathology (AREA)
  • Brushes (AREA)
  • Laminated Bodies (AREA)
  • Paints Or Removers (AREA)
  • Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)

Abstract

Matériau de revêtement à activité antimicrobienne prolongée qui comporte une solution de résine multipolymère de nylon, d'acide et d'ammonium quaternaire de silane, et utilisation dudit matériau de revêtement pour conférer une protection antimicrobienne à un article préalablement corrodé à l'acide et recouvert dudit matériau.
PCT/US1993/011406 1992-12-04 1993-11-24 Traitement de surface antimicrobien durable de materiaux plastiques Ceased WO1994013748A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU56759/94A AU5675994A (en) 1992-12-04 1993-11-24 Durable antimicrobial surface treatment of plastic materials

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US98538592A 1992-12-04 1992-12-04
US07/985,385 1992-12-04

Publications (1)

Publication Number Publication Date
WO1994013748A1 true WO1994013748A1 (fr) 1994-06-23

Family

ID=25531430

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1993/011406 Ceased WO1994013748A1 (fr) 1992-12-04 1993-11-24 Traitement de surface antimicrobien durable de materiaux plastiques

Country Status (4)

Country Link
AU (1) AU5675994A (fr)
EC (1) ECSP931005A (fr)
MX (1) MX9307478A (fr)
WO (1) WO1994013748A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6420455B1 (en) 1999-06-18 2002-07-16 3M Innovative Properties Company Antimicrobial composition containing photosensitizers articles, and methods of use
WO2002072672A3 (fr) * 2001-03-14 2003-03-06 Du Pont Solutions de multipolymeres de nylon a duree de conservation accrue
US6572926B1 (en) 1997-12-23 2003-06-03 Biosafe, Inc. Biostatic product using interpenetrating network polymers
DE10141599B4 (de) * 2000-08-31 2004-08-05 Arteva Technologies S.A.R.L. Permanente, antimikrobielle Beschichtung für Kunststoffasern und entsprechendes Beschichtungsverfahren
US7851653B2 (en) 2005-03-22 2010-12-14 Biosafe, Inc. Method of creating a solvent-free polymeric silicon-containing quaternary ammonium antimicrobial agent having superior sustained antimicrobial properties

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1795686A1 (de) * 1963-05-31 1973-05-24 Monsanto Co Modifiziertes polyamid
JPS5986632A (ja) * 1982-11-09 1984-05-18 Toyobo Co Ltd 抗菌処理方法
WO1986003214A1 (fr) * 1984-11-21 1986-06-05 Stamicarbon B.V. Melanges de resine polyamide
EP0424548A1 (fr) * 1988-10-13 1991-05-02 BASF Lacke + Farben AG Solutions de laques adhésives fusibles, stables au stockage

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1795686A1 (de) * 1963-05-31 1973-05-24 Monsanto Co Modifiziertes polyamid
JPS5986632A (ja) * 1982-11-09 1984-05-18 Toyobo Co Ltd 抗菌処理方法
WO1986003214A1 (fr) * 1984-11-21 1986-06-05 Stamicarbon B.V. Melanges de resine polyamide
EP0424548A1 (fr) * 1988-10-13 1991-05-02 BASF Lacke + Farben AG Solutions de laques adhésives fusibles, stables au stockage

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 008, no. 193 (C - 241) 5 September 1984 (1984-09-05) *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6572926B1 (en) 1997-12-23 2003-06-03 Biosafe, Inc. Biostatic product using interpenetrating network polymers
US6420455B1 (en) 1999-06-18 2002-07-16 3M Innovative Properties Company Antimicrobial composition containing photosensitizers articles, and methods of use
DE10141599B4 (de) * 2000-08-31 2004-08-05 Arteva Technologies S.A.R.L. Permanente, antimikrobielle Beschichtung für Kunststoffasern und entsprechendes Beschichtungsverfahren
WO2002072672A3 (fr) * 2001-03-14 2003-03-06 Du Pont Solutions de multipolymeres de nylon a duree de conservation accrue
US7851653B2 (en) 2005-03-22 2010-12-14 Biosafe, Inc. Method of creating a solvent-free polymeric silicon-containing quaternary ammonium antimicrobial agent having superior sustained antimicrobial properties
US7858141B2 (en) 2005-03-22 2010-12-28 Biosafe Inc. Method of creating a sustained silicon-containing quaternary ammonium antimicrobial agent within a polymeric material

Also Published As

Publication number Publication date
AU5675994A (en) 1994-07-04
ECSP931005A (es) 1994-08-15
MX9307478A (es) 1994-08-31

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